Both Castlehead and Friar’s Crag are right near town. Castlehead was a little steep especially at the end and there was a little bit of rock scrambling but it was worth it for the views.
It was sometimes challenging to figure out exactly where the path was in all the leaves under the trees, but it didn’t much matter. Once you crossed over the road near Friar’s Crag it was much easier to see.
The walk from Castlehead to Friar’s Crag goes along the shore of Derwent Water.
Friar’s Crag is much easier (it’s basically flat and paved) and had almost as good a view so you could just do that one and skip the effort.